Heat the oven to 400°F. Line a large baking sheet with parchment paper. Use two sheets if needed so the squash is not crowded.
Add the cubed squash to a large bowl. Drizzle with the olive oil and maple syrup, then sprinkle with the salt, cinnamon, and pepper. Toss until every piece is coated.
Spread the squash in a single layer, leaving a little space between the cubes.
Roast for 15 minutes. Flip the pieces, then roast for 15 to 20 minutes more, until the centers are fork tender and the edges are golden brown.
Taste and add a pinch more salt if needed. Serve warm or at room temperature.